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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N5O7P
Molecular Weight 347.2216
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADENOSINE PHOSPHATE

SMILES

C([C@]1([H])[C@]([H])([C@]([H])([C@]([H])(n2cnc3c(N)ncnc32)O1)O)O)OP(=O)(O)O

InChI

InChIKey=UDMBCSSLTHHNCD-KQYNXXCUSA-N
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12614440 | https://clinicaltrials.gov/ct2/show/NCT00179010

Adenosine monophosphate (AMP) is a nucleotide, consisting of a phosphate group, the sugar ribose, and the nucleobase adenine. AMP is an activator of several enzymes in the tissues. In the glycolytic pathway, the enzyme phosphofructokinase is inhibited by ATP but the inhibition is reversed by AMP, the deciding factor for the reaction being the ratio between ATP and AMP. In medicine, AMP is used mainly as an alternative to adenosine for treatment of ischemia and as a tool compound to measure hyperresponsiveness of airways.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21589
Gene ID: 4907.0
Gene Symbol: NT5E
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Functional and molecular characterization of receptor subtypes mediating coronary microvascular dilation to adenosine.
2001 Feb
The phosphodiesterase inhibitors pentoxifylline and rolipram suppress macrophage activation and nitric oxide production in vitro and in vivo.
2001 Feb
Characterization of a G protein-coupled receptor for nicotinic acid.
2001 Feb
Peptones stimulate intestinal cholecystokinin gene transcription via cyclic adenosine monophosphate response element-binding factors.
2001 Feb
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms.
2001 Feb
PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells.
2001 Feb
C2-ceramide and reactive oxygen species inhibit pituitary adenylate cyclase activating polypeptide (PACAP)-induced cyclic-AMP-dependent signalling pathway.
2001 Feb
Orexin A stimulates cortisol secretion from human adrenocortical cells through activation of the adenylate cyclase-dependent signaling cascade.
2001 Feb
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001 Feb
Structural analysis of adenylate cyclases from Trypanosoma brucei in their monomeric state.
2001 Feb 1
Brief treatments with forskolin enhance s-phase entry in balance epithelia from the ears of rats.
2001 Feb 1
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001 Feb 2
C-type natriuretic peptide has a negative inotropic effect on cardiac myocytes.
2001 Feb 2
Expression of type I adenylyl cyclase in intrinsic pathways of the hippocampal formation of the macaque (Macaca nemestrina).
2001 Feb 23
Prostaglandin E2 and vasoactive intestinal peptide increase vascular endothelial cell growth factor mRNAs in lung cancer cells.
2001 Feb-Mar
Differential coupling of the human P2Y(11) receptor to phospholipase C and adenylyl cyclase.
2001 Jan
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.
2001 Jan
Peptidergic modulation of an insect Na(+) current: role of protein kinase A and protein kinase C.
2001 Jan
cAMP-dependent presynaptic regulation of spontaneous glycinergic IPSCs in mechanically dissociated rat spinal cord neurons.
2001 Jan
Effects of prostaglandin E2 and cAMP elevating drugs on GM-CSF release by cultured human airway smooth muscle cells. Relevance to asthma therapy.
2001 Jan
Regulation of TNF-alpha-induced eotaxin release from cultured human airway smooth muscle cells by beta2-agonists and corticosteroids.
2001 Jan
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.
2001 Jan
A novel transverse push-pull microprobe: in vitro characterization and in vivo demonstration of the enzymatic production of adenosine in the spinal cord dorsal horn.
2001 Jan
Tubulin stimulates adenylyl cyclase activity in C6 glioma cells by bypassing the beta-adrenergic receptor: a potential mechanism of G protein activation.
2001 Jan
AgRP(83-132) acts as an inverse agonist on the human-melanocortin-4 receptor.
2001 Jan
Glucose enhances adenylyl cyclase responses in normal but not diabetic GK rat islets.
2001 Jan
Effects of cilostazol on late lumen loss and repeat revascularization after Palmaz-Schatz coronary stent implantation.
2001 Jan
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.
2001 Jan
Prostaglandin E(2)-induced interleukin-6 release by a human airway epithelial cell line.
2001 Jan
Nitric oxide attenuates H(2)O(2)-induced endothelial barrier dysfunction: mechanisms of protection.
2001 Jan
Expression of different phosphodiesterase genes in human cavernous smooth muscle.
2001 Jan
Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid.
2001 Jan
Identification of rat H3 receptor isoforms with different brain expression and signaling properties.
2001 Jan
Differential alterations in cardiac adrenergic signaling in chronic hypoxia or norepinephrine infusion.
2001 Jan
A new hypoglycemic agent, JTT-608, evokes protein kinase A-mediated Ca(2+) signaling in rat islet beta-cells: strict regulation by glucose, link to insulin release, and cooperation with glucagon-like peptide-1(7-36)amide and pituitary adenylate cyclase-activating polypeptide.
2001 Jan
Localization and mechanisms of action of cannabinoid receptors at the glutamatergic synapses of the mouse nucleus accumbens.
2001 Jan 1
Role of stimulatory guanine nucleotide binding protein (GSalpha) in proliferation of PC-3M prostate cancer cells.
2001 Jan 1
Chemical coding of intrinsic and extrinsic nerves in the guinea pig gallbladder: distributions of PACAP and orphanin FQ.
2001 Jan 1
Pituitary adenylate cyclase activating peptide (PACAP) in the enteropancreatic innervation.
2001 Jan 1
Simultaneous measurements of intracellular cAMP and L-type Ca2+ current in single frog ventricular myocytes.
2001 Jan 1
Porcine Choroid plexus epithelial cells in culture: regulation of barrier properties and transport processes.
2001 Jan 1
Gangliosides GD1b, GT1b, and GQ1b enhance IL-2 and IFN-gamma production and suppress IL-4 and IL-5 production in phytohemagglutinin-stimulated human T cells.
2001 Jan 1
The relationship between differentiation and survival in PC12 cells treated with cyclic adenosine monophosphate in the presence of epidermal growth factor or nerve growth factor.
2001 Jan 12
Vasoactive intestinal peptide-stimulated adenosine 3',5'-cyclic monophosphate formation in cerebral cortex and hypothalamus of chick and rat: comparison of the chicken and mammalian peptide.
2001 Jan 12
Cloning and sequence of the LYS2 homologue gene from the osmotolerant yeast Pichia sorbitophila.
2001 Jan 15
Cerebroprotective action of a Na+/Ca2+ channel blocker NS-7. I. Effect on the cerebral infarction and edema at the acute stage of permanent middle cerebral artery occlusion in rats.
2001 Jan 26
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.
2001 Jan 26
Hypothalamic orexin-A binding sites are downregulated by chronic nicotine treatment in the rat.
2001 Jan 26
Neurohormonal regulation of secretion from isolated rat stomach ECL cells: a critical reappraisal.
2001 Mar 2
The human VPAC1 receptor: three-dimensional model and mutagenesis of the N-terminal domain.
2001 Mar 30
Patents

Sample Use Guides

In clinical studies for treatment of Ichemia, adenosine monophosphate is administered by intraaterial infusion of AMP at 3 different doses for 15 minutes each (at equimolar doses as adenosine). As a tool to measure hyperresponsiveness of airways, AMP was administered internasally.
Route of Administration: Other
In Vitro Use Guide
To measure activity of 5’-nucleotidase, lymphocytes from peripheral blood were incubated with [G-3H]adenosine 5'-monophosphate. Aliquots were removed after 0, 15, 30, and 60 min of incubation without shaking. The cells were washed twice with phosphate buffered saline. The cells were dissolved in 7 ml of Aquasol, and the radioactivity was determined in a scintillation counter.
Name Type Language
ADENOSINE PHOSPHATE
HSDB   INCI   INN   MART.   USAN   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
A 5MP
Code English
ADENOSINE PHOSPHATE [INN]
Common Name English
NSC-20264
Code English
ADENOSINE 5'-(DIHYDROGEN PHOSPHATE).
Common Name English
ADENOSINE 5'-MONOPHOSPHATE
Systematic Name English
5'-ADENYLIC ACID [USP-RS]
Common Name English
ADENOSINE PHOSPHATE [INCI]
Common Name English
A-5MP
Code English
ADENOSINE PHOSPHATE [MART.]
Common Name English
ADENOSINE PHOSPHATE [USAN]
Common Name English
ADENOSINE PHOSPHATE [VANDF]
Common Name English
5'-ADENYLIC ACID
FCC   MI   USP-RS  
Systematic Name English
ADENOSINE PHOSPHATE [HSDB]
Common Name English
ADENOSINE PHOSPHATE [WHO-DD]
Common Name English
AMP
Common Name English
5'-ADENYLIC ACID [MI]
Common Name English
5'-ADENYLIC ACID [FCC]
Common Name English
ADENYL
Brand Name English
ADENOSINE MONOPHOSPHATE
Systematic Name English
Classification Tree Code System Code
DSLD 3633 (Number of products:8)
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
NCI_THESAURUS C709
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
Code System Code Type Description
HSDB
3281
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
EPA CompTox
61-19-8
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
RXCUI
309
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
ADENOSINE MONOPHOSPHATE
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
USP_CATALOG
1012178
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY USP-RS
CAS
53624-78-5
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
SUPERSEDED
NCI_THESAURUS
C83606
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-500-0
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
PUBCHEM
6083
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
MERCK INDEX
M1416
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY Merck Index
FDA UNII
415SHH325A
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
MESH
D000249
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
CAS
61-19-8
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
ChEMBL
CHEMBL752
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
DRUG CENTRAL
92
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
EVMPD
SUB05267MIG
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
INN
335
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY
DRUG BANK
DB00131
Created by admin on Sat Jun 26 02:35:51 UTC 2021 , Edited by admin on Sat Jun 26 02:35:51 UTC 2021
PRIMARY